The structure of pyrenophorin

Nozoe, Shigeo; Hirai, Koichi; Tsuda, Kyosuke; Ishibashi, Keijiro; Shirasaka, Makoto; Grove, John Frederick

doi:10.1016/s0040-4039(01)84033-8

Cited by 83 publications

(42 citation statements)

References 2 publications

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“…1 H NMR spectroscopic analyzes (300 MHz, CDCl 3 ) and 13 C NMR (75.49 MHz, CDCl 3 ) showed a structure of the compound of R t 13.4 min, being probably the isoxazole 9.…”

Section: Resultsmentioning

confidence: 98%

“…The probes used were ATB and SW, with 5 mm internal diameter, at room temperature with 45° pulse for hydrogen and carbon. Chemical displacements (d) in 1 The isomeric mixture of 9-oxabicyclo[3.3.1]nonane-2,6-diol (3) and 9-oxabicyclo[4.2.1]nonane-2,5-diol (3a) was prepared by the oxidation of cycloocta-5-diene (2) (1.18 mol) under treatment with formic acid [9][10][11] (1.06 mol) and under vigorous magnetic stirring and, in an ice bath, 30% H 2 O 2 (300 mL, 9.20 mol) was added dropwise. After the addition, the formation of a biphasic mixture was observed, which was maintained at 50 °C (internal temperature).…”

Section: General Methodsmentioning

confidence: 99%

“…Following the research conducted in our laboratory to obtain macrocyclic lactones, it was developed the synthesis of a precursor that will be later applied to the racemic synthesis of the natural 16-membered macrolide pyrenephorin 1 (1), a macrolactone dimer with high biological potential ( Figure 1). …”

Section: Introductionmentioning

confidence: 99%

“…The bioactive metabolite 1, pyrephorin, was isolated from the pathogenic fungi Pyrenophora avenae and Stemphylium radicinum, 1 and the cultures of Drechslera avenae acting as a phytotoxin on leaves segments of Avena sterilis. 2 In as much of the wide spectrum of biological activities, mainly as antibiotics, several synthetic methodologies for the synthesis of this 16-member macrolide, racemic or chiral, have been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin

Costa¹,

Martins²,

ARAUJO³

et al. 2017

J. Braz. Chem. Soc.

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A convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy manipulation, 9-oxabicyclo[3.3.1]nonane-2,6-diol, for the preparation of the bicyclic intermediate, which sequentially was subjected to oxidative cleavage with butyl nitrite resulted in an isomeric mixture, a dioximedilactone and diisoxazoledilactone.

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“…1 H NMR spectroscopic analyzes (300 MHz, CDCl 3 ) and 13 C NMR (75.49 MHz, CDCl 3 ) showed a structure of the compound of R t 13.4 min, being probably the isoxazole 9.…”

Section: Resultsmentioning

confidence: 98%

Section: General Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin

Costa¹,

Martins²,

ARAUJO³

et al. 2017

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…These macrodiolides are classified into two groups; one includes homodimers that consist of two identical units, and the other includes heterodimers that consist of two different units. Macrodiolides such as pyrenophorol (1), 1 pyrenophorin (2), 2 and vermiculine (3), 3 which have 16-membered rings are homodimeric macrodiolides, and macrocylic dilactones such as colletallol (4) 4 and grahamimycin A1, which have 14-membered rings, are heterodimeric macrolides (Fig. 1).…”

mentioning

confidence: 99%